Organometallic additions to beta-substituted N-boc-beta-aminoaldehydes: a new synthesis of enantiomerically pure 1,3-disubstituted N-boc-1,3-aminoalcohols

摘要

1,2-addition of organolithium and organomagnesium derivatives to beta-substituted (N-Boc)-beta-aminoaldehydes gave access to enantiomerically pure, 1,3-disubstituted, 1,3-aminoalcohols. A diastereoselective version of this addition was also investigated and Gilman cuprates were found to add onto aldehydes 1a-b with notable diastereoselectivity (up to 70% de) in favour of the anti isomer. The absolute configuration of each obtained 1,3-aminoalcohol was determined. (C) 2000 Elsevier Science Ltd. All rights reserved. [References: 40]